The Third
by angeldoggy2007
Summary: Jenny has succeeded in becoming friends with Blaire and Serena, but now she has to pursuade the last and third of the three... Sophia Castellano.  Good luck Jenny.  Gossip Girl, you know you love me.....
1. Challenge

My first fan-fic using this story, so bear with me if I get stuff wrong...

I don't own, Gossip Girl, or any of the characters, except one in this story.

angeldoggy2007

You know you love me.

_

* * *

_

_Good Morning Upper East Siders, _

_Gossip Girl here, your one way ticket into the scandalous lives of Manhattan's most richest and spoiled._

_The top story on my home page?_

_Looks like the three musketeers are going to be reunited._

_That's right folks, Sophia Castellano is back._

_Blaire and Serena's third friend has finally returned from three years of studying abroad in England, she practically has all the colleges in her sixty-thousand dollar ring wearing hand._

_But being away has kept her from knowing about Serena and Blaire's little feud, and as they have agreed, she doesn't have to know._

_What Sophia doesn't know, won't hurt her right?_

_Although that little feud isn't the only thing that's new..._

_The newbie, little Jenny Humphrey, has joined the whole enterouze_

_And Sophia had just found out that Jenny has passed Blaire and Serena's judgment._

_Surprised? Oh yes she is._

_But little does Jenny know she has to convince the last, third and smartest of the three, to finally be with the 'in' crowd._

_And it's not going to be easy, my sources tell me they met briefly on Saturday at a brunch:

* * *

_Sophia is talking with Chuck, he is informing her about the new news around Manhatten, and who are they talking about? Jenny.

Speak of the devil because enters Jenny in her new, hard-to-walk in Jimmy Choos, courtesy of Blaire, she manages to trip on on of the charis and bumps into, whoops, Sophia--

Who just happens to be carrying a glass of early morning wine, Jenny is lucky enough that she didn't get on Sophia's dark navy, Perre Beglio, A La Couture, worth way more than the Humphrey's loft...and all of their cars.

Chuck smirks at Sophia's annoyed expression, Sophia turns to look at Jenny, her fake smile in place, Chuck steps up next to her, poor Jenny could only stare at the two of New York's most wealthiest people.

"Sophia," Chuck smiles evilly at Jenny, "This is Jenny the one everyone's been talking about."

Jenny still in shock, manages to form a sentence, "H-hi, nice to meet you."

Sophia surveys Jenny for a second, and smirks, "Mmm." she says dismissively.

Chuck, is containing his laughter, "I'll let you to get to know each other..." he says as he's walking away, no doubt going to pick up another slut.

Jenny looks after him out of disbelief, she turns to look at Sophia, whose expression has changed, she's smiling, and this one actually looks as real as an L.V. straight from Italy itself.

"Jenny," she starts, "Humphrey. Right?"

Jenny can only nod.

"I've met you're brother, you know, the one going out with Serena?" she continues, "Nice guy, a little plain, but good for the new Serena, I guess."

"Oh," Jenny says.

"Enough about him, you're... the new one," Sophia says promptly, "Jenny Humphrey." then despite where they are she starts walking around Jenny, as if inspecting her, "Has a crush on Serena's little brother, almost was raped by Chuck, but was saved by Serena and Dan."

She stopped in front of her, "Congrats."

"For what?" Jenny finally looks her in the eye.

"For being the new 'It' girl of course," she smiles, "Winning over Serena and Blair. You're quite lucky. You got Serena because of her new personality and Blaire because of your... services."

"Oh no, I-I'm not an--" Jenny begins.

"But a little word of advice," cutting off Jenny as she leans in so she can whisper in her ear, "You're not in until you're in," she raises her perfectly plucked (not to mention waxed) eyebrows.

"What's that suppose to mean?" Jenny asks suddenly finding her courage back.

Sophia's smile turns sweet again when they heard, "Miss Castellano!!!"it was the mayor of Manhattan, again, wishing to bid her a good morning and welcome back. Sophia turns to go greet them, as she walks away she turns to look at Jenny, "Good luck impressing me Freshman...and walking in those shoes."

Jenny is so surprised she didn't move for five minutes, the only thing she knew and was thinking about was that, her work still wasn't done...

* * *

_Oh yes Jenny._

_You're not done yet._

_Will Jenny keep going to finally be with the 'In' crowd and will she succeed? _

_Or will she crack under pressure and fail miserably, then run home to their four-bedroom loft, with her tail between her legs?_

_We're all just dying to find out._

_One things for sure._

_The result will be as rewarding as a eight-hundred thousand dollar shopping spree in Milan._

_xoxoXOXO Gossip Girl XOXOxoxo_

_You know you love me...

* * *

_Please comment!!! 


	2. Lies

_Good Morning Upper Eastsiders, _

_Gossip Girl here._

_Your first-class ticket into the lives where if you're rich and have connections, you get what you want; all wrapped up in a cute little Coach bag ready for the taking._

_Te juiciest scoop of the day?_

_Serena and Blair are having a little reunion party for Sophia on Saturday night, three days from now, anyone who matters is going to be there, including moi of course. And a certain little freshman we know..._

_It was supposed to be a surprise, so naturally Sophia finds out-- about the party and Jenny's invite:_

* * *

They're in Blair's apartment, for their traditional, brunch together, watching "Breakfast at Tiffany's", in comes Jenny, with Krispy Kremes, she obviously doesn't know that Blair was on a strict diet for the party. 

"H-hey guys!" she says breathlessly, "I brought donuts!!!"

Serena smiles a weak smile, knowing what's about to come, "Hey Jenny."

No one else responds, poor Jenny just stands there with her Abercrombie & Fitch jacket, standing in the door way, until Blair, annoyed that the cold wind is blowing in, tosses her hair, "God, plant your ass on that couch and close the door." she rolls her eyes.

"Okay, donuts?" she tries again.

Sophia finally acknowledges her, "Jenny sweetie, Blair's on a diet remember?" she says sweetly.

Ding! Jenny remembers and just sits down, burning red, there's about ten minutes of awkward silence, until--

"So, Blair what are you wearing at the party on Saturday?" Jenny says to break the ice, "Jeans? Or a plaid skirt?"

Oops, bad idea Jenny, Blair rolls her eyes and flips her hair, "It's formal Jenny," she scoffs.

"Oh," looks like Jenny has to whip up another gown...asap.

"And if you must know, I'm wearing, Christina Perrin." Blair turns back to her nails.

"Really? Which one?" Serena inputs.

"Oh, she's custom designing it for me..." Blair responds absently.

"Mmm, if you're going to wear Perrin, I'll wear, Sonja Rykiel." says Sophia, "her black will match with Perrin's winter collection, what about you Serena?"

"Well, if we're all going as black then I'll go with Donatella Versace," Serena smiles, "What about you Jenny?"

"Uh, Armani?" Jenny squeaks.

"Ugh, getting too, raggedy Ann. But whatever, it's black." Blair frowns.

"Blair, don't get aging lines just because little miss Brooklyn here can't decide what to wear, relax," Sophia pats her friend, "I don't mind if just one person stands out." Then she turns to Jenny, "Where what you want, we don't care."

"It's okay, I have some black gowns," Jenny retorts.

"If you say so," Sophia shrugs, "But, you'll still need at date."

Ooh Jenny, good luck replying to that one, "I-I have a friend coming over from Chicago, he'll be my date, he's super cute." Jenny quickly sprouts.

"Hot, Jenny, he's hot," Serena reminds her.

"Right! Hot! Yeah, he's super hot and his name is, uh, Justin."

"Right," Blair scoffs, "Then, we'll see him at the party."

"Uh, I just remembered, I have to help Dan with something, bye!" she jumps up and runs out the door.

Blair and Serena are looking after her, while Sophia is smirking at the window; it was going to take more than a little butt-kissing to earn her trust anytime, Jenny was going to find that out soon enough.

* * *

_Looks like Jenny has gotten herself into a huge bad pickle, we're talking about wearing-last-year's-clothes bad._

_Poor Jenny, where will she find her date from Chicago? Will she finally be able to gain Sophia's trust?_

_We're all just dying to find out._

_You better stay tuned to find out._

_xoxoXOXO Gossip Girl XOXOxoxo_

_You know you love me..._


	3. Brunch

_Good Morning UpperEastsiders,_

_Gossip Girl Here,_

_You're first class ticket into the juiciest lives of Manhattan's most elite._

_The top story on my homepage?_

_Jenny frantically tries to find her "hot date" from Chicago, we're talking going to bars, other parties, almost going, as a last resort, online dating. That girl is desperate to find one just to become with the 'in' crowd. _

_And she's about to catch a break._

_Her father's best friend just happens to have a son coming home from going to Oxford, no one has ever seen him or known him. Rumor is that he was the top students there... Although it didn't matter if he was the nerdiest guy there to Jenny, she just had to get him as a date._

_Luckily her father and his friend had scheduled at brunch on Sunday morning..._

_

* * *

_

Jenny's getting ready to meet with her father and his best friend, she and Dan are going to be there, as will her future date.

For casual wear Jenny put on a dress length, strapless top and jeans with a pair of comfy flats--

Hey if Blair, Serena or Sophia aren't going to be there, why go formal?

She gets a ride in a taxi to the designated restaurant, small, casual, comfy, but unfortunately for Jenny it's nice enough to have a brunch for two, very good listeners... Blair's somewhat loyal groupies; Isabel Coastes and Kati Farkas.

Ooh Jenny, how are you going to get a date without letting the chatter boxes know?

"Hey guys!" Jenny smiles, trying not to show how nervous she was, "Why are you here?"

They both look at Jenny as if she's crazy, "We were called here, gossip girl told us something was waiting for us to come here, speaking of which did you get invited here too?"

"No, I'm just meeting my date for the upcoming party for Sophia, he's should be here--"

"Incoming!" Kati says.

Jenny looks behind them to see what they were staring at, it turns out a gorgeous guy was coming in, dark curly hair, green eyes, Abercrombie worthy figure...

"Ooh, hotie alert, was this what gossip girl was talking about?" Isabel whispers. Jenny stares too until she realizes, that her father's best friend had just come in with him, well hello.

"Excuse me ladies," Jenny says politely, she then walks up to them, "Hello Mr. Stevenson! I'm Jenny, Rufus Humphrey's daughter."

Mr. Stevenson smiles, "Yes, I remember when you were young, Jennifer, allow me to introduce you to my son, Will." The green eyed god, Adonis(Jenny says) smiles at her, "Nice to meet you Jennifer."

"Jenny," she then takes that time to turn to the two gossip columns, there faces are filled with envy, mission accomplished.

"Where is your father Jennifer?" asked Mr. Stevenson.

"Oh he must be on his way-- so how long are you guys staying?" she asks as they sit down to there assigned table.

"Just two weeks then we're going back to California.." another point for Jenny, Sophia's party was only a week away. "Oh, then would you like me to give Will a chance to see the city?"

"Uh, well your father said that Dan would be." Mr. Stevenson said confused. Jenny cursed in her mind, she had completely forgotten about her brother, "Well, Dan just got a new girlfriend so I don't think he'll be able to--"

"Arnold!" calls a voice, Jenny sees her dad coming to the table, "Sorry, traffic was murder. How are you?"

Jenny glares at her dad, who doesn't notice, she tries to engage herself in a conversation with Will, hoping that Isabel and Kati would believe they were life long friends.

She would try to get him as her date somehow...

* * *

_Sorry Jenny, I couldn't help myself, playing with you is so much fun..._

_Will Jenny actually get Will as her date before time runs out?_

_My platinum Gucci watch is ticking Jenny and time will eventually run out..._

_Stick around to watch if Jenny can get herself out of this deep pit, as for me, I can't wait so see the charm our little freshman can pull off on her yummy guest from California._

_If so happen Jenny fails, I could always dump my date..._

_xoxoXOXO Gossip Girl XOXOxoxo_

_You know you love me._


	4. Two Words: Par Tay

_Good morning upper-eastsiders,_

_Gossip Girl here._

_Well, I'm back, after a long break, try rehab--_

_Jk, Jk._

_Sorry girls (and boys), I have been too busy with preparations for Sophia's little party, and as you all know 'little' means roughly 200 people. Oh yes, so many people to impress, so little time to prepare._

_But it was all worth it._

_It seems that dark lighting's and heavy music does set a sexy mood and with that comes dirt. I'm not talking about Chuck hooking up with another stripper dirt..._

_Mmhmm, I barely finished my first apple martini, when the drama started, ha, talk about fast._

_Anyway, enough about me, I've got the inside scoop about what happened at the party--_

* * *

Jenny strode into the double door entrance to the club _Zins,_ behind her walked in a confused Will.

"Jenny? What's this, I thought you were taking me to the Hayden Planetarium." he frowned. Jenny sighed, maybe bribing her brother (paying for his car wash) and getting this English exchange student as a date, wasn't the smartest thing to do.

However from the corner of her eye she could see Isabel and Kati gaping at her and Will.

That was all the encouragement she needed as she whirled to look at Will, putting on her best pout, "Listen will, I was going to take us there but they were closed, so I brought us here instead! What a way to meet people!" she giggled coyly, charm was a way to mans heart right?

"Could I just return to the hotel?" he asked, his nose scrunched up, clearly the boy wasn't the brightest crayon in the box. At least that would him shield him from any interested singles in here-- girls AND guys.

"No!" she screamed but recovered, "Please? I want to meet you to some of my friends, we'll even see Dan's girlfriend, Serena.. So please?" she put on a begging face, the one she had seen Blaire use on her father, well an attempt of it anyway.

"Fine," he shrugged as he squint, looking through the crowds. _Okay, I just got to let Blaire see him, but not Sophia, she'll chew him alive and found out everything!, _Jenny thought.

"Okay, you stay over there at the bar while I look for them.." she motioned to a stool and turned, pushing her way through the crowds, until she reached the area where Blaire was chatting with some upper class friends.

"H-hi Blaire!" Jenny breathed.

She saw Blaire stiffen and say, "Excuse me girls.." and turned to her.

"What?" she snapped, "Jenny, my rule is when I'm talking to other people, don't come up to me!" Jenny bit her lip and took a step back, "Look I'm sorry I want you to meet Will."

"Who?"

"Remember, the friend that I told you was coming to visit? From England?"

"Wasn't it Justin from Chicago?" said a voice from behind her, Jenny turned to see-- oh shit, Sophia, as pretty as hell. Staring at her with her perfectly done eyes.

"Uh, it was going to be, but he canceled, something about going to California. So I called over Will he's one of my, uh, many connections...,Jenny quickly stammered the lie.

"Right," Sophia smiled, that was just as believable as a sterling silver necklace **(A/N Fake or Cheap silver)** she walked past Jenny and squeezed her friend 'Hello', "Blaire!" and kissed Blaire on the cheek, twice, once on each side.

"I love the party, so many people that I haven't seen for so long!" she gushed, fittingly, she waved and blew a kiss to someone else in the crowd.

"Thanks," smiled the pleased host, "Have you seen Nate?"

"Yeah, over by the bar, talking to some yummy British dude." Serena said coming from behind holding hands with Dan.

"What?" Jenny screamed, and ran back to the bar, _Oh no, oh no, what if someone finds out??, _she thought miserably.

Sure enough, one of the sexiest teen in Manhattan and the British tourist were engaged in a conversation.

Jenny ran over to them, managing to get to them in record time (especially with those two inch Jimmy Choos), "Will!" she squeaked.

"Hey Jenny, this is Nate." Will said casually, not knowing what Jenny's current situation was like.

"Hey Jenny," Nate smiled, Jenny gaped, _How much does he know??_, Jenny worried as Blaire walked over to him and gave him a peck 'hello'.

"Yeah hi, Will--"

"Oh so you know this guy Jenny?" Sophia called from behind. Jenny froze, and turned with a fake smile plastered on her face, "H-hey Sophia, yeah, this is Will. Will this is Sophia Castellano one of my... friends."

"More like accquaintances..." Sophia corrected as she walked closer, her eyes suddenly alluring, "Hello Will."

"H-hi," Will stammered whose eyes widened when he saw the gorgeous enemy.

_Oh shit_, Jenny thought.

* * *

_That's all for today children--_

_But don't whine or worry, more will becoming soon... With any luck._

_Ooh this gets juicier by the second:_

_Will Jenny be found out? How much does Nate know? Will Sophia crack the foreigner, exploit Jenny? And cause the freshman to fall from her newly found spot?_

_We're all just dying to find out..._

_One things for sure, Manhattan's got the dirtiest dirt to spread and as long as that's going on, I'll always be here._

_xoxoXOXO Gossip Girl XOXOxoxo_

_You know you love me..._


End file.
